


Sexual Play at the Playground

by seraphina_iclyn



Category: Supernatural
Genre: Dean Winchester - Freeform, F/M, Sexual Content, Supernatural - Freeform, dean-reader makeout, dean-reader sex, explicit - Freeform, make out, reader - Freeform
Language: English
Status: Completed
Published: 2015-05-27
Updated: 2015-05-30
Packaged: 2018-04-01 11:17:17
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 4
Words: 3,887
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/4017730
Author URL: https://archiveofourown.org/users/seraphina_iclyn/pseuds/seraphina_iclyn
Summary: <blockquote class="userstuff">
              <p>You meet Dean as he stops in to your work as a bartender. Before you know it, you are off to the park for a make out session.</p>
            </blockquote>





	1. At the Playground

**Author's Note:**

> In later chapters, Dean and the reader will go further.  
> In this work, I assume that the reader is a female. Sorry to any guys that may offend. If anyone wants a Dean and Male Reader story, let me know, I am open to writing one.
> 
>  
> 
> ****Although this is my work, I did not create the character Dean. I do not mean to take credit for Dean or anything else related to Supernatural and its actual owners.

He came to you at work, dressed differently than the usual clientele. Suit, tie, and badge. Asked you all about those strange deaths. They say that bartenders know everything that goes on in a town, and sure, you typically know what happened, but customers don't exactly admit to murder.

Although you don't know anything the FBI man asked, you would let him interrogate you any time. You couldn't get passed that ruggedness underneath the suit. And you could have sworn that you saw him wink at you. But no, he couldn't have. The G-man was very serious about getting answers, not about getting to know you. You've seen hundreds of hotties as a bartender, but he was something different.

….

That was two days ago. In a moment of pure stereotype, you absentmindedly wipe down the bar. You hear the bell at the top of the entrance make the tinkling noise it does when people come in or go out. You look up to him again, no suit, no tie, and no badge. This time he is in jeans, a t shirt, and a loose, unbuttoned shirt with the sleeves rolled up.

Before you know it he's sitting in front of you.

"Can I get a beer?" he asks in his gruff voice.

You nod because you seem to have lost yours. As you bring him his drink , your hands just barely touch. This makes him snap out of his thoughts and look right at you.

Just an agent working a case, you remind yourself. You feel your muscles tighten as his eyes seem to look at you, and through you, at the same time. Do not flirt with him.

"Hi," he said as he smiled and winked at you.

Immediately you feel your cheeks flush and your muscles get tighter.

"Hey," you answer leaning in to him so that you could get closer. The bar still divides you, but that extra inch helps relieve some of the tension building within you. "Aside from the case, are you enjoying your stay in town?"

"It's something, that's for sure" he answered. It seemed like he was momentarily brought to some less than pleasant thought.

"Have you at least had any fun?"

"No, but I'd like to have a little before I leave."

Please let me be that fun, you plead in your mind. You smile and gently bite your lip; hoping that if you bite your lip the pleading will stay in your mind. As you do this, you swear he scooted the bar stool up closer.

"Any-uh- recommendations?" he asks raising the bottle to his lips.

Ugh, those lips. Never before have you wanted to be a beer bottle. Just to be pressed against those lips.

He snaps you out of your reverie, "know anyone I should see?"

Without thinking, a whispered "me" slipped out of you. Crap, you think, too far.

"When do you get off work?"

"An hour, but is it okay for us to be seen together with the case and everything?" Can you even date a federal agent mid case?

"I will see you then. And by the way, the case? It's over. So you can call me Dean," he answers as in one swift motion he gets up, slaps money on the bar, and walks out the door.

Okay then, you say to yourself. Stunned. And after a moment you realize... Dean isn't the name he gave you before.

....

That was the longest hour of work ever. But you are so excited to see him leaning against a black car.

Hot guy, hot car you thought. But first things first, this name change thing. You ask him, and without kissing a beat he tells you that his agent name is different from his real one to protect his identity.

Reasonable enough...

You hop in his car. As the engine roars to life, some classic rock comes on the radio and you can't help but nod along.

"So where should we go?" Dean asks you from the driver's seat.

You direct Dean to a park on the edge of town. The park is fairly secluded and not many people go there, let alone after dark. But this is your special place. You love going here.Like a kid, you run straight to the swings. Trying to look mature, you reign yourself in and simply sit on the swing. To your surprise, Dean sits in the next swing over. For a while you two chat, small talk mostly, and nothing of real significance.

After a while, Dean gets up and walks behind you. He grabs the chains of the swing and starts swinging you gently. Each time you swing back at him, your heart leaps as you catch a whiff of his cologne. As the conversation continues, Dean slows the swing down little by little until he has one hand around the swing chain and one hand on your waist.

You turn to look at him, and find him leaning in closer to you. You lean in to him as best you can, since you're still seated on the swing and just looking back at him.

Then it happens: that delicious moment where he closes the gap between his mouth and yours. The rugged looking hottie kisses you faintly and gently. It is almost as though he is afraid of your reaction, but he still has to kiss you. All too soon, the kiss is over. Now that he has kissed you, you know that there is some interest there, so you can’t just leave it at one light kiss.

You get up from the swing and kiss him. This time, there is no swing in the way. You are both standing this time, so you can press your entire body against his. You kiss him gently at first, just because he kissed you doesn't mean he wants a full out make out session. You slowly rais the intensity of your kisses, and he matches your energy each time.

He can kiss, that guy. Before you know it, his hand is sliding down your back, and he kisses a trail from your lips to your neck. Your body tightens, even though you can feel yourself melting into him at the same time. You can feel a cool breeze blow through the park, making the goosebumps on your skin more pronounced. At the same time, it makes the heat between the two of you more intense.

"You okay with this?" Dean asks in a gruff and whispered tone.

"Yes," you whisper in answer.

And with your answer, Dean leads you to the nearby slide.Gently, he lays you down on the cool plastic of the slide. Once you are laying against the incline of the slide, Dean begin to crawl over you. He holds his weight on his forearms above your shoulders. The rest of his body rests partially on you and partially on his left leg; he is half on you and half on the slide. He slowly lowers his face down to yours and begins kissing you again. With his right hand, Dean gently touches your face and then runs his hand down your neck to your chest. His first touch on your breast is gentle, but then you let out a small moan and he runs with it. Dean begins applying more pressure as he cups your breast. Clearly not a person to leave a job half done, he moves on to the other side. After a few minutes of labored breathing and chest fondling, Dean’s hand begins to move lower.You can’t help but squirm as his hand skims your abdomen. 

At the snap for your jeans, he pauses, as though asking for permission. You have been anticipating his touch down there since he began to moved his hand down. 

“Oh, god, please… don’t stop now…” you gasp.

“Are you sure?” he asks you. You can tell he wants a yes, but still wants to respect your boundaries.

“Yes!” you whisper shout. you can’t help yourself, you push his hand down into your crotch. You need him to know that you need him to keep going.

You hear him chuckle, and then get right to business. The way he applies pressure is unreal. You can’t help but wriggle beneath him. The more you wiggle, the more he pushes into you with his body weight, but it doesn’t feel like too much weight. Before you know it, you feel his mouth move from yours. He scoots down the slide and traces his path with kisses. When his kisses reach the snap of your jeans, he lifts up your shirt and kisses his way back up to your chest. When he gets back to your breasts he lifts your shirt and bra to reveal your breasts completely. He begins to tease your newly exposed skin with his tongue and light nips of his teeth. 

In an effort to stay still so that you can fully enjoy what he does to you, you dig your fingers ever so slightly into his back. you could swear that you hear him groan ever so slightly, and that kills any hope you have of being subdued. You wrap your fingers into his short tousled hair and gently pull him back up to your face. You kissed him fiercely, moaning into his mouth. 

“Can I take you back to my motel room?” Dean asks you.

You nod in return; both excited to take this to a bed and sad that you’re going to have to stop to get there. Slowly, Dean stands back up, grabs your hand, and helps pull you back up. Like a true gentleman, he helps you pull your shirt and bra back down and in the correct position. On the way back to his motel, you can tell Dean is speeding- not enough to make you scared, but enough so that you can tell he is desperate to take you to bed.


	2. Exploring Dean with Your Tongue

**Summary for the Chapter:**

> You reach Dean's motel room, play a little, and then you move to satisfy Dean.

**Notes for the Chapter:**

> This is a continuation of Sexual Play at the Playground.
> 
> The reader is assumed to be a female. If anyone would like me to create a DeanXMale reader story let me know.
> 
> No copyright infringement is intended. I don't own the character of Dean. I'm just having fun with him.

Last Chapter: You nod in return; both excited to take this to a bed and sad that you’re going to have to stop to get there. Slowly, Dean stands back up, grabs your hand, and helps pull you back up. Like a true gentleman, he helps you pull your shirt and bra back down and in the correct position. On the way back to his motel, you can tell Dean is speeding- not enough to make you scared, but enough so that you can tell he is desperate to take you to bed. 

 

You finally reach the motel, and Dean leads you to room on the second floor. It feels like forever going to his room. He lead you by gently wrapping his arm around you waste to point you in the right direction.You are still catching your breath from the make out session on the slide. Dean, on the other hand, seems perfectly controlled. You begin to doubt just how into this he is; perhaps this isn’t a big deal to him, maybe he does this all the time. You are nervous because this isn’t exactly your nature, but this guy gives you vibes like you have never felt before.

Your doubts dissolve within the first two seconds of being in Dean’s motel room. As soon as the door shuts, Dean picks you up at the waist and holds you between himself and the wall. You wrap your legs around him. With your legs around him, Dean is free to move his hands from your waist. He places his hands on the sides of your face. After a few minutes of kissing this way, Dean takes a step back away from the door.To make sure you don’t fall, Dean supports you with one arm around you and another under your butt. You keep your legs wrapped around his waist and your arms around his neck. The six feet from the door to the bed went quickly because the two of you never stop kissing. 

At the bed, Dean lays you down. He slowly takes off the shirt with the rolled up sleeves, revealing a tight t-shirt and amazing arm muscles. You can’t help but gasp as he lifts his t-shirt to remove it. With his shirts off, Dean motions for you to sit up. He tugs at the bottom of your t-shirt, and you remove it. As you do so, Dean kneels in front of you. He uses those strong arms of his to pull you closer to the edge of the bed. He then undoes the snap of your jeans and begins to tug them off of you. Once your pants are off, Dean gets off of his knees and stands in front of you. He is only a few inches away, and you look up at him. You can hear his slightly hitched breathing. You take initiative and grab his hips and pull him the rest of the way to you. Taking advantage of this proximity you kiss him below his navel and just above his belt buckle. After applying a light kiss, you move to undo his belt. With the buckle undone, you pull to slide the belt out of the loops. When you manage to free his belt, you toss it to the floor. Your heart beat quickens with each step closer to seeing the rest of Dean’s body. You undo his pants; first the snap, and then the zipper. Pulling his pants down, you are finally able to get a closer look at the final prize: Dean’s package. Through the thin layer of his boxers, you are able to see the large bulge. Dean breaks your focus when he moves to step out of the jeans now resting at his ankles.

Dean in only his boxers, jumps on the bed and rests on his side. You are only in your bra and panties and waste no time meeting Dean in the middle of the bed. You begin kissing and leaning into each other. He reaches around you and unhooks your bra in a fluid motion. You push against his shoulder, guiding Dean to lay on his back. You get on your knees and remove your bra. Then you move to straddle Dean, and bend down to kiss him.You begin to grind your crotch against his hard member. Dean puts his hands on your hips, guiding your grinding. He takes advantage of your closeness during the peak of a thrust and catches one of your nipples in his teeth, biting down ever so gently.

You gasp. Dean moves his teeth further down your nipple and swirls his tongue around your tip of your nipple. As he teases you harder, you grind on his dick with more pressure. Dean pinches and gently twists your other nipple. You kiss him, and then begin to kiss a trail down his neck. Following your direction, Dean eases off of your breasts and lets go of your hips. You slide down Dean’s body, trailing kisses along the way. When you get to the waist of his boxers, you pull them down, and are careful to bring the elastic up and around his dick. You continue to scoot down until you remove Dean’s boxers completely. After tossing Dean’s boxers to the floor you make your way back up from the foot of the bed. You take a few seconds to admire the nakedness laying before you. Dean is undeniably hot and certainly well off. 

You see Dean bite his lip as he looks at you, and he is clearly not nervous about the situation. Dean is still laying on his back, so you climb up on the bed and kneel between his legs. You then bend forward bringing your mouth as close to his cock as possible without actually touching it.You hear Dean exhale a sexually frustrated breath and smirk when you raise your eyes to meet his. You start by running the tip of your tongue from the base to the tip of his dick. When you reach the tip, you take his cock into your mouth. You begin to explore every inch of Dean’s package with your tongue. You have never enjoyed giving a blow job as much as you are enjoying it right now. You keep sucking and swirling your tongue around Dean until he cums. When Dean’s breathing gets under control from his orgasm all he can manage to say is, “fuck.”

Stay tuned for the next chapter, aka: your turn.


	3. Your Turn

**Summary for the Chapter:**

> After you take care of Dean, it's your turn for him to go down on you.

**Notes for the Chapter:**

> The reader is assumed to be female. If there is anyone who wants me to do a story with Dean and a male reader, let me know.
> 
> No infringement intended. I do not own the character Dean, I am just having fun with him.

Last Chapter: You see Dean bite his lip as he looks at you, and he is clearly not nervous about the situation. Dean is still laying on his back, so you climb up on the bed and kneel between his legs. You then bend forward bringing your mouth as close to his cock as possible without actually touching it.You hear Dean exhale a sexually frustrated breath and smirk when you raise your eyes to meet his. You start by running the tip of your tongue from the base to the tip of his dick. When you reach the tip, you take his cock into your mouth. You begin to explore every inch of Dean’s package with your tongue. You have never enjoyed giving a blow job as much as you are enjoying it right now. You keep sucking and swirling your tongue around Dean until he cums. When Dean’s breathing gets under control from his orgasm all he can manage to say is, “fuck.”

“Okay, baby, your turn,” Dean pants as he repositions the two of you so you are on your back and he is sitting on the bed next to you. The excitement of Dean taking care of you is overwhelming, but you would still just be happy to keep staring at the naked hottie.He gets up off of the bed and grabs you by your ankles and pulls you to the end of the bed. When your butt reaches the edge of the bed, he stops. Then he pulls your panties off of you and tosses them aside.He spreads your legs and kneels between them. He kisses you on the top edge of your labia. “Not yet,” he says.

You groan and he chuckles. He climbs back on the bed next you. He lays on his side, supporting himself on his left arm, he runs his hand up and down your torso. It tickles and arouses you at the same time. Dean then leans down and begins playing with your nipples again, this time he uses such light effort that you can barely feel it. This is all a part of his plan to wind you up. He runs his hands on and around your breasts and down to the heat between your legs. Even on your lady bits, Dean uses gently and barely there pressure. At this point you are both moaning with pleasure and whimpering with impatience. He begins to plant light kisses on your stomach. Your breath hitches. Then all of the sudden his demeanor changes, and Dean begins to kiss you like he can’t get enough of you. As he kisses you from your breasts to your waistline, you can feel yourself getting further riled up. You wonder if you might actual cum without him ever touching your clit or penetrating you. 

“Are you ready?” Dean asks you. He does not wait for an answer before kissing his way down to your lady zone. He stops in the same spot he kissed in the beginning at the top of your labia. He then gets off of the bed and kneels between your legs. He positions you so that your knees are on his shoulders, and the rest of your legs are dangling behind his back. 

 

He leans into you, and gently blows a stream of air up and down the length of your femininity. He then plants kisses all around your opening. And then it happened. He went all out. Kissing, licking, and gently sucking on your warmth until you reach your peak.As you bein to shake as you lose control, Dean holds you still so that you are forced to feel every intense wave of pleasure. You have never felt so completely pleasured before, you can’t catch your breath and your legs are shaking. Dean climbs back onto the bed next to you smirking with satisfaction from your reaction. You look at him again, first in his desire filled eyes, and then you notice that once again he is rock hard.

Stay tuned for the next chapter: the big event.


	4. Going All the Way

**Summary for the Chapter:**

> You and Dean finally reach full out sex

**Notes for the Chapter:**

> It is assumed the reader is a woman, if there is anyone who wants a guy reader version, let me know.
> 
> No infringement intended. I don't own the character of Dean. I am just having fun playing with him.

Last chapter: He leans into you, and gently blows a stream of air up and down the length of your femininity. He then plants kisses all around your opening. And then it happened. He went all out. Kissing, licking, and gently sucking on your warmth until you reach your peak. As you begin to shake as you lose control, Dean holds you still so that you are forced to feel every intense wave of pleasure. You have never felt so completely pleasured before, you can’t catch your breath and your legs are shaking. Dean climbs back onto the bed next to you smirking with satisfaction from your reaction. You look at him again, first in his desire filled eyes, and then you notice that once again he is rock hard.

Dean leans in and kisses you, pulling your body against his.He pulls you close enough so that your bodies are fully pressed against each other. You can feel his erection pressing into you, and you can feel the stickiness of his excitement on your skin. He rolls on top of you while kissing you, and in one swift motion he is between your legs. There is still space between you because he is sort of hovering above you. You grab his sides and pull him down to you. Dean begins kissing your neck as he lowers himself, and you can tell he is preparing to enter you. 

And the moment you have been waiting for arrives. With a slow but deliberate movement, Dean puts himself inside of you. You gasp as he fills you, and your tightness makes Dean let out a soft moan as well. Slowly, Dean begins thrusting. He picks up the pace as time goes on, and he bends down to kiss you which helps to muffle the loud moans that are probably disturbing nearby motel guests. You don’t care though, you are having too much fun. Dean slides up with each thrust, rubbing your clit along the way. Your pleasure builds, and Dean goes harder and faster.

Just when you think you are about to go over the edge, Dean stops. He grabs one of the pillows at the head of the bed and places it under your butt. He enters you again. The simple change makes Dean hit all new angles and you quickly begin to get close to climax again. You shudder as you experience your orgasm. Dean continues thrusting until you finish. In a few more thrusts Dean pulls out of you and finishes himself outside of you, seeing as you just now realize neither of you brought up protection. 

Spent, Dean flops down next to you and you both fall into a fitful sleep.


End file.
